data_CRYSTALS_cif _audit_creation_date 07-11-23 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.5516(5) _cell_length_b 11.7085(4) _cell_length_c 16.9923(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2696.15(17) _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'P n m a ' _symmetry_space_group_name_Hall '?' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x+1/2,y+1/2,z+1/2' 'x+1/2,-y+1/2,-z+1/2' 'x,-y+1/2,z' '-x,y+1/2,-z' '-x+1/2,-y,z+1/2' 'x+1/2,y,-z+1/2' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Rh -1.1178 0.9187 19.2957 0.7515 14.3501 8.2176 4.7343 25.8749 1.2892 98.6062 5.3280 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C19 H18 Cl4 F3 N4 O5 Rh1 S1 # Dc = 1.76 Fooo = 1424.00 Mu = 11.66 M = 358.08 # Found Formula = C19 H18 Cl4 F3 N4 O5 Rh1 S1 # Dc = 1.76 FOOO = 1424.00 Mu = 11.66 M = 358.08 _chemical_formula_sum 'C19 H18 Cl4 F3 N4 O5 Rh1 S1' _chemical_formula_moiety 'C16 H14 N4 O2 Rh, C F3 O3 S, 2(C H2 Cl2)' _chemical_compound_source ? _chemical_formula_weight 716.15 _cell_measurement_reflns_used 7562 _cell_measurement_theta_min 3 _cell_measurement_theta_max 29 _cell_measurement_temperature 180 _exptl_crystal_description 'planar' _exptl_crystal_colour 'yellow' _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.764 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 1.166 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.84 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 180 _diffrn_reflns_number 28592 _reflns_number_total 3723 _diffrn_reflns_av_R_equivalents 0.072 # Number of reflections with Friedels Law is 3723 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4785 _diffrn_reflns_theta_min 2.830 _diffrn_reflns_theta_max 32.264 _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 30.974 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min 0 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.43 _refine_diff_density_max 0.59 _refine_ls_number_reflns 1803 _refine_ls_number_restraints 6 _refine_ls_number_parameters 180 #_refine_ls_R_factor_ref 0.0285 _refine_ls_wR_factor_ref 0.0302 _refine_ls_goodness_of_fit_ref 1.1211 #_reflns_number_all 4792 _refine_ls_R_factor_all 0.0932 _refine_ls_wR_factor_all 0.0640 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.7\s(I) _reflns_number_gt 1803 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_gt 0.0302 _refine_ls_shift/su_max 0.001235 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration '.' _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.405 -0.158E-01 0.188 ; # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; ; _publ_contact_author_name 'Yves Canac' _publ_contact_author_address ; Laboratoire de Chimie de Coordination 205 route de Narbonne 31077 Toulouse Cedex 04, FRANCE ; _publ_contact_author_phone '' _publ_contact_author_fax '' _publ_contact_author_email 'yves.canac@lcc-toulouse.fr' _publ_requested_journal 'JACS' _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name '' _publ_section_title # Title of paper - generally just the systematic or trivial name ; Diaminocarbene and phosphonium ylide ligands: a systematic comparison of their ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Yves Canac.' # Author 1 ; Laboratoire de Chimie de Coordination 205 route de Narbonne 31077 Toulouse Cedex 04, FRANCE ; ; ? # Footnote for author 1 ; 'Christine Lepetit' # Author 2 ; Laboratoire de Chimie de Coordination 205 route de Narbonne 31077 Toulouse Cedex 04, FRANCE ; ; ? # Footnote 2 ; 'Mohammed Abdalilah' # Author 2 ; Laboratoire de Chimie de Coordination 205 route de Narbonne 31077 Toulouse Cedex 04, FRANCE ; ; ? # Footnote 2 ; 'Carine Duhayon' # Author 2 ; Laboratoire de Chimie de Coordination 205 route de Narbonne 31077 Toulouse Cedex 04, FRANCE ; ; ? # Footnote 2 ; 'Remi Chauvin' # Author 2 ; Laboratoire de Chimie de Coordination 205 route de Narbonne 31077 Toulouse Cedex 04, FRANCE ; ; ? # Footnote 2 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; The H atoms were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens H111 H 0.2241 0.7500 0.5513 0.0642 1.0000 Uiso RS . . . . . H112 H 0.1445 0.7500 0.4821 0.0640 1.0000 Uiso RS . . . . . C11 C 0.1542(5) 0.750000(6) 0.5382(4) 0.0549 1.0000 Uani S T . . . . Rh1 Rh 0.69634(3) 0.7500 0.53085(2) 0.0251 1.0000 Uani S T . . . . C1 C 0.6911(3) 0.6355(3) 0.62091(18) 0.0243 1.0000 Uani . . . . . . C2 C 0.6329(3) 0.5334(3) 0.7236(2) 0.0285 1.0000 Uani . . . . . . C3 C 0.7211(3) 0.4914(3) 0.7045(2) 0.0319 1.0000 Uani . . . . . . C4 C 0.8520(3) 0.5394(4) 0.6060(3) 0.0482 1.0000 Uani . . . . . . C5 C 0.5270(2) 0.6901(3) 0.67387(19) 0.0235 1.0000 Uani . . . . . . C6 C 0.4374(2) 0.6322(3) 0.6783(2) 0.0300 1.0000 Uani . . . . . . C7 C 0.3498(3) 0.6908(3) 0.6839(2) 0.0344 1.0000 Uani . . . . . . C8 C 0.6997(3) 0.6344(3) 0.4525(2) 0.0336 1.0000 Uani . . . . . . N1 N 0.6149(2) 0.6248(2) 0.67324(16) 0.0234 1.0000 Uani . . . . . . N2 N 0.7558(2) 0.5544(2) 0.64218(18) 0.0294 1.0000 Uani . . . . . . O1 O 0.7025(3) 0.5672(2) 0.40589(16) 0.0554 1.0000 Uani . . . . . . H21 H 0.5900 0.5082 0.7638 0.0344 1.0000 Uiso R . . . . . H31 H 0.7541 0.4321 0.7295 0.0392 1.0000 Uiso R . . . . . H41 H 0.8932 0.4920 0.6380 0.0725 1.0000 Uiso R . . . . . H42 H 0.8451 0.5053 0.5552 0.0723 1.0000 Uiso R . . . . . H43 H 0.8840 0.6121 0.6004 0.0726 1.0000 Uiso R . . . . . H61 H 0.4373 0.5521 0.6774 0.0339 1.0000 Uiso R . . . . . H71 H 0.2900 0.6501 0.6869 0.0423 1.0000 Uiso R . . . . . Cl2 Cl 0.10251(14) 0.87376(18) 0.57599(11) 0.1021 1.0000 Uani . . . . . . C9 C 0.4546(4) 0.7500 0.1499(4) 0.0405 1.0000 Uani S T . . . . C10 C 0.4098(6) 0.750000(6) 0.4056(4) 0.0556 1.0000 Uani S T . . . . O2 O 0.5571(2) 0.8534(2) 0.25445(18) 0.0430 1.0000 Uani . . . . . . O3 O 0.6439(3) 0.7500 0.1528(2) 0.0377 1.0000 Uani S T . . . . S1 S 0.56600(9) 0.7500 0.20982(8) 0.0275 1.0000 Uani S T . . . . F1 F 0.3737(3) 0.7500 0.1945(3) 0.0627 1.0000 Uani S T . . . . F2 F 0.4496(2) 0.6583(3) 0.10500(18) 0.0699 1.0000 Uani . . . . . . H101 H 0.4669 0.7500 0.3701 0.0701 1.0000 Uiso RS . . . . . H102 H 0.3497 0.7500 0.3755 0.0701 1.0000 Uiso RS . . . . . Cl1 Cl 0.41477(12) 0.87351(11) 0.46283(8) 0.0720 1.0000 Uani . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.047(3) 0.085(5) 0.032(3) 0.0000 -0.002(3) 0.0000 Rh1 0.02727(18) 0.02147(15) 0.02647(17) 0.0000 0.0028(2) 0.0000 C1 0.0233(15) 0.0202(13) 0.0294(16) -0.0025(12) -0.0029(16) 0.0021(16) C2 0.0338(19) 0.0222(15) 0.0295(17) 0.0067(13) -0.0021(15) -0.0031(15) C3 0.037(2) 0.0236(15) 0.0352(18) 0.0067(15) -0.0075(15) 0.0035(15) C4 0.037(2) 0.051(3) 0.056(3) 0.010(2) 0.013(2) 0.020(2) C5 0.0233(16) 0.0235(15) 0.0239(15) 0.0004(13) -0.0014(13) 0.0001(14) C6 0.0281(18) 0.0278(16) 0.0341(18) 0.0032(15) -0.0015(16) -0.0042(15) C7 0.0228(17) 0.044(2) 0.037(2) 0.0013(17) 0.0044(16) -0.0078(16) C8 0.0378(19) 0.0293(16) 0.034(2) -0.0018(13) 0.0012(19) -0.0045(19) N1 0.0232(14) 0.0185(12) 0.0286(14) 0.0014(11) -0.0013(12) -0.0014(11) N2 0.0303(16) 0.0240(14) 0.0338(15) 0.0017(12) 0.0000(13) 0.0034(13) O1 0.078(2) 0.0431(15) 0.0450(15) -0.0177(14) -0.0057(18) -0.0017(19) Cl2 0.0971(13) 0.1182(14) 0.0909(12) -0.0449(11) 0.0015(10) 0.0184(11) C9 0.032(3) 0.036(3) 0.054(4) 0.0000 -0.002(3) 0.0000 C10 0.075(5) 0.056(4) 0.036(3) 0.0000 0.007(3) 0.0000 O2 0.0446(16) 0.0320(12) 0.0524(16) -0.0121(14) 0.0082(13) -0.0035(14) O3 0.034(2) 0.038(2) 0.041(2) 0.0000 0.0090(18) 0.0000 S1 0.0281(7) 0.0209(5) 0.0333(6) 0.0000 0.0060(5) 0.0000 F1 0.0296(18) 0.072(3) 0.086(3) 0.0000 0.007(2) 0.0000 F2 0.0592(17) 0.0694(18) 0.081(2) -0.0325(16) -0.0224(15) -0.0015(15) Cl1 0.0990(10) 0.0603(7) 0.0568(7) -0.0134(7) -0.0112(8) 0.0186(7) _refine_ls_extinction_method 'None' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag H111 . C11 . 0.973 no H112 . C11 . 0.963 no C11 . Cl2 5_565 1.733(4) yes C11 . Cl2 . 1.733(4) yes Rh1 . C1 5_565 2.036(3) yes Rh1 . C8 5_565 1.899(3) yes Rh1 . C1 . 2.036(3) yes Rh1 . C8 . 1.899(3) yes C1 . N1 . 1.368(4) yes C1 . N2 . 1.343(4) yes C2 . C3 . 1.333(5) yes C2 . N1 . 1.392(4) yes C2 . H21 . 0.944 no C3 . N2 . 1.374(4) yes C3 . H31 . 0.929 no C4 . N2 . 1.452(5) yes C4 . H41 . 0.956 no C4 . H42 . 0.957 no C4 . H43 . 0.960 no C5 . C5 5_565 1.402(6) yes C5 . C6 . 1.392(5) yes C5 . N1 . 1.416(4) yes C6 . C7 . 1.375(5) yes C6 . H61 . 0.939 no C7 . C7 5_565 1.387(8) yes C7 . H71 . 0.941 no C8 . O1 . 1.117(4) yes C9 . F2 5_565 1.319(4) yes C9 . S1 . 1.822(6) yes C9 . F1 . 1.332(7) yes C9 . F2 . 1.319(4) yes C10 . Cl1 5_565 1.744(4) yes C10 . H101 . 0.981 no C10 . H102 . 0.961 no C10 . Cl1 . 1.744(4) yes O2 . S1 . 1.434(3) yes O3 . S1 . 1.433(4) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl2 5_565 C11 . H111 . 108.0 no Cl2 5_565 C11 . H112 . 108.1 no H111 . C11 . H112 . 111.1 no Cl2 5_565 C11 . Cl2 . 113.5(4) yes H111 . C11 . Cl2 . 108.0 no H112 . C11 . Cl2 . 108.1 no C1 5_565 Rh1 . C8 5_565 93.36(12) yes C1 5_565 Rh1 . C1 . 82.37(17) yes C8 5_565 Rh1 . C1 . 175.71(14) yes C1 5_565 Rh1 . C8 . 175.71(14) yes C8 5_565 Rh1 . C8 . 90.9(2) yes C1 . Rh1 . C8 . 93.36(12) yes Rh1 . C1 . N1 . 125.1(2) yes Rh1 . C1 . N2 . 130.2(3) yes N1 . C1 . N2 . 104.7(3) yes C3 . C2 . N1 . 106.9(3) yes C3 . C2 . H21 . 127.8 no N1 . C2 . H21 . 125.2 no C2 . C3 . N2 . 107.2(3) yes C2 . C3 . H31 . 126.6 no N2 . C3 . H31 . 126.1 no N2 . C4 . H41 . 110.7 no N2 . C4 . H42 . 110.2 no H41 . C4 . H42 . 109.1 no N2 . C4 . H43 . 109.9 no H41 . C4 . H43 . 107.9 no H42 . C4 . H43 . 108.9 no C5 5_565 C5 . C6 . 119.14(19) yes C5 5_565 C5 . N1 . 122.70(16) yes C6 . C5 . N1 . 118.1(3) yes C5 . C6 . C7 . 120.9(3) yes C5 . C6 . H61 . 119.2 no C7 . C6 . H61 . 119.9 no C7 5_565 C7 . C6 . 119.9(2) yes C7 5_565 C7 . H71 . 120.4 no C6 . C7 . H71 . 119.7 no Rh1 . C8 . O1 . 179.2(4) yes C5 . N1 . C2 . 123.9(3) yes C5 . N1 . C1 . 126.2(3) yes C2 . N1 . C1 . 109.7(3) yes C4 . N2 . C3 . 124.7(3) yes C4 . N2 . C1 . 123.9(3) yes C3 . N2 . C1 . 111.3(3) yes F2 5_565 C9 . S1 . 111.4(3) yes F2 5_565 C9 . F1 . 106.7(3) yes S1 . C9 . F1 . 111.3(4) yes F2 5_565 C9 . F2 . 109.1(5) yes S1 . C9 . F2 . 111.4(3) yes F1 . C9 . F2 . 106.7(3) yes Cl1 5_565 C10 . H101 . 108.2 no Cl1 5_565 C10 . H102 . 109.2 no H101 . C10 . H102 . 110.0 no Cl1 5_565 C10 . Cl1 . 112.0(4) yes H101 . C10 . Cl1 . 108.2 no H102 . C10 . Cl1 . 109.2 no C9 . S1 . O2 5_565 103.05(17) yes C9 . S1 . O2 . 103.05(17) yes O2 5_565 S1 . O2 . 115.2(3) yes C9 . S1 . O3 . 103.4(3) yes O2 5_565 S1 . O3 . 114.83(14) yes O2 . S1 . O3 . 114.83(14) yes